(1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethan-1-ol

Base Information

Chemical Name:(1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethan-1-ol
CAS No.:1308324-58-4
Molecular Formula:C₁₅H₂₂O₄
Molecular Weight:266.337
Hs Code.:

Synonyms:(1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethan-1-ol

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Chemical Property of (1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethan-1-ol

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Technology Process of (1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethan-1-ol

There total 4 articles about (1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethan-1-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

: 1308324-57-3
C₂₂H₂₈O₇S

: 1308324-58-4
(1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethan-1-ol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 3h; Reflux; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.02.010

Reference yield:

: 81028-12-8
(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

: 1308324-58-4
(1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethan-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 - 20 °C / Inert atmosphere

1.2: 0.75 h / -78 °C / Inert atmosphere

2.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 48 h / 20 °C / Inert atmosphere

3.1: dmap; di(n-butyl)tin oxide; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Reflux; Inert atmosphere

With dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; water; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; acetone;
DOI:10.1016/j.tetasy.2011.02.010

Reference yield:

: 1308324-56-2
(1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethane-1,2-diol

: 1308324-58-4
(1S)-1-{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethan-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: dmap; di(n-butyl)tin oxide; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Reflux; Inert atmosphere

With dmap; lithium aluminium tetrahydride; di(n-butyl)tin oxide; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetasy.2011.02.010